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Crossdressing advice
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Hello, I'll probably get slatted for this, but after some advise. I started a relationship 18 weeks ago with a woman, we have been social bubbling and are starting to explore my kinks and she has discovered some of my toys which she would love to try with me, this includes a double ended dildo. However how do I approach the fact I enjoy receiving anal and obviously how to do in conversation that I like to crossdress.
She has said she wants to explore my deepest darkest desires and that I should tell them her, but I fear this might be a bit too much. Any help would be very much appreciated and thank you in advance.
Love John/Sara xxx |
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By (user no longer on site)
over a year ago
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Personally I’d just be straight and honest with her as in tell her what you like to do wear but allow her enough wiggle room to say fuck yea or maybe just not yet.
Best of luck op!!
T |
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By (user no longer on site)
over a year ago
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if its a part of your life, you owe her to tell her, how would you feel if she kept something from you?
its the only right thing to do, and if it goes wrong then she istnt the one for you, but i would imagine she probably already knows |
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Better to tell her sooner rather than later. If she does not like it, and I think you might be surprised, then you are not for each other. It will come out in the end. i told my last GF and she enjoyed it and even bought me some nice lingerie. |
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By (user no longer on site)
over a year ago
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"Hello, I'll probably get slatted for this, but after some advise. I started a relationship 18 weeks ago with a woman, we have been social bubbling and are starting to explore my kinks and she has discovered some of my toys which she would love to try with me, this includes a double ended dildo. However how do I approach the fact I enjoy receiving anal and obviously how to do in conversation that I like to crossdress.
She has said she wants to explore my deepest darkest desires and that I should tell them her, but I fear this might be a bit too much. Any help would be very much appreciated and thank you in advance.
Love John/Sara xxx"
You need to be straight with her, like andy said would you like it if she kept something from you? Imagine the fun you could have once she knows, all the shopping too!!! I know its a different situation but i found out about my dad being a crossdresser when he passed, it's nothing to be ashamed of, i would have loved to have known about my dad. |
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By (user no longer on site)
over a year ago
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Just tell her, life is too short and she's clearly open minded.
Maybe try wearing ladies underwear as a suprise to introduce her to it rather than go all in to begin with. |
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By (user no longer on site)
over a year ago
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"Hello, I'll probably get slatted for this, but after some advise. I started a relationship 18 weeks ago with a woman, we have been social bubbling and are starting to explore my kinks and she has discovered some of my toys which she would love to try with me, this includes a double ended dildo. However how do I approach the fact I enjoy receiving anal and obviously how to do in conversation that I like to crossdress.
She has said she wants to explore my deepest darkest desires and that I should tell them her, but I fear this might be a bit too much. Any help would be very much appreciated and thank you in advance.
Love John/Sara xxx"
If she has already asked you to show her, Show her  |
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By (user no longer on site)
over a year ago
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Ahh it's the dream of many TVs on here to find a long term partner who is in tune...or even likes to play and encourage crossdressing.
I can understand your dilemma in this if you have a good relationship that is working now as 1 it gets even better or 2 it all ends suddenly.
Whatever you do OP...good luck  |
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By (user no longer on site)
over a year ago
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"Ahh it's the dream of many TVs on here to find a long term partner who is in tune...or even likes to play and encourage crossdressing.
I can understand your dilemma in this if you have a good relationship that is working now as 1 it gets even better or 2 it all ends suddenly.
Whatever you do OP...good luck "
It's not my dream but yes good luck OP Xx |
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By (user no longer on site)
over a year ago
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Best bet is to be truthful and honest but if you feel you can’t for fear off ending the relationship then try this
When in the bed room and clothes are off get up to go to the toilet make shour her bra is in sight on the floor pick it up and jokeingly say how does this look on me or something and see what her reaction is
If it’s good sit down and talk to her if it’s bad
Or if you can’t bring ur self to tell her
Please for the love off god end it with her
She dosent need to be hurt 4-5 years down the line
There one more option and that’s to walk away form the life all to gether and don’t tell her at all and never come back to it
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By (user no longer on site)
over a year ago
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OP I would guess that she already has some idea. She’s already suggested sharing your toys and by asking you to share your desires she’s opening up Pandora’s box.
Be brave, be open, honesty is always best.
I wouldn’t change my relationship with Abby for anything. We’ve had a lot of challenges and some soul searching but it’s made our partnership stronger.
Good luck!
Miss V |
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By (user no longer on site)
over a year ago
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Living a secret is never going to end well, you place a distance between yourself and herself and won’t ever become close if you don’t open up.
You actually have the invite to do so, you have everything to gain and someone who obviously trusts you enough... there’s risks but you’ll never have a better person to try to be open with x |
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By (user no longer on site)
over a year ago
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Get her to tell you her secrets first..you may find she's wanted to have fun with a cross dresser. I dont see anything particularly disturbing about wanting to use a dildo on your arse. So you could talk about arse play and see if she likes anal fun. You could then open up discussion about wanting to feel like a woman when you are getting fucked with a dildo.. And lead into it that way. To be honest the fact that she is the one bringing this up seems a big signal that she has kinky things she wants to admit to you to see if you are adventurous... So sounds like a very good sign to me |
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This is like turning an oil tanker, nice and slow.
It might be a bit dishonest and sly but I would try to make it her think it's all her idea. A casual remark here and there, talk of lingerie while your out. A suggestion of buying something for her, then say how turned on you felt picturing her wearing it, that you found it sexy buying it. Play on it, say while choosing your gift you felt left out as women have so much to choose from, styles, materials, ask her how it feels next to the skin, how it feels to have something to hold your body and how it gives her confidence to flaunt herself.
When you have sex with her in that lingerie take time to look at her in it, make her show you, make her feel extra sexy, trace the outlines of it with your finger tips, make a part of you both! Always mention how lucky women are to have such sexy clothes to wear!
Give the conversations some direction and let her take the lead, hopefully she would suggest you try something, be creative and ready for 'her idea' !!
Tell her how stimulated you was when you wore something she gave you to try, how sex became higher, if you lucky you could progress the dressing, let her lead and think it's all her doing.
A slow progress but worth it, never push but be easily lead!!
Good luck!! |
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Five long term relationship with women, five times I’ve had the conversation with them about my crossdressing. Pick the right moment, so not when she’s just going out to work. Then the right words and ally any fears she has about it, try to focus on the positive and it should go ok. No need to get to complicated.
Non of the women I told finished with me over it. They just wanted different levels of participation  |
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My partner cross dress he just started to tell me went we were just together for about 6 months he told me he like wearing stockings and knickers and as we got further in to our relationship he started tell me he won like too try nightly etc and stuff and we be together nearly 7 years together |
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By (user no longer on site)
over a year ago
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"Hello, I'll probably get slatted for this, but after some advise. I started a relationship 18 weeks ago with a woman, we have been social bubbling and are starting to explore my kinks and she has discovered some of my toys which she would love to try with me, this includes a double ended dildo. However how do I approach the fact I enjoy receiving anal and obviously how to do in conversation that I like to crossdress.
She has said she wants to explore my deepest darkest desires and that I should tell them her, but I fear this might be a bit too much. Any help would be very much appreciated and thank you in advance.
Love John/Sara xxx"
You are so lucky that she is bringing this up now, go for it! When I was married my wife loved my dressing. Tasmin |
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